US4060469A - Preparation of 1,1,1-trifluoro-2,2-dichloroethane - Google Patents

Preparation of 1,1,1-trifluoro-2,2-dichloroethane Download PDF

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US4060469A
US4060469A US05/753,155 US75315576A US4060469A US 4060469 A US4060469 A US 4060469A US 75315576 A US75315576 A US 75315576A US 4060469 A US4060469 A US 4060469A
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trifluoro
chlorine
reaction zone
dichloroethane
chloroethane
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US05/753,155
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Richard F. Sweeney
James O. Peterson
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Allied Corp
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Allied Chemical Corp
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Priority to CA293,040A priority patent/CA1076148A/en
Priority to FR7737679A priority patent/FR2375164A1/en
Priority to DE19772755828 priority patent/DE2755828A1/en
Priority to IT69847/77A priority patent/IT1093049B/en
Priority to JP15250877A priority patent/JPS5382711A/en
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122—Incoherent waves
    • B01J19/123—Ultraviolet light
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms

Definitions

  • the present invention relates to a process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane, namely, CF 3 CHCl 2 , and, more especially, relates to the preparation of 1,1,1-trifluoro-2,2-dichloroethane by the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane [CF 3 CH 2 Cl] under certain critically defined reaction parameters.
  • 1,1,1-TRIFLUORO-2,2-DICHLOROETHANE IS A KNOWN COMPOUND.
  • This chlorofluorocarbon is of value as an aerosol propellant, particularly as a stratospherically safe aerosol propellant.
  • thermal chlorination of 1,1,1-trifluoro-2-chloroethane too has been described in the prior art. Compare E. T. McBee et al, Ind. & Engineering Chem., 39, 409 (1947), wherein the thermal chlorination of 1,1,1-trifluoroethane [CF 3 CH 3 ] has been shown to proceed in the following stepwise manner:
  • reaction sequence [ii] can be said to represent the chlorination of interest.
  • Another object of the invention is to provide a process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane by the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane under certain critically defined reaction conditions.
  • Yet another object of the invention is to provide for the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane under such critically defined reaction conditions as to provide high yields of 1,1,1-trifluoro-2,2-dichloroethane with concomitant minimal [less than about 1%] by-production of the perhalogenated compound, 1,1,1-trifluoro-2,2,2-trichloroethane.
  • the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane can unexpectedly be conducted such as to provide high yields of 1,1,1-trifluoro-2,2-dichloroethane, with only minimal amounts [less than about 1 mole percent] of by-product 1,1,1-trifluoro-2,2,2-trichloroethane, by contacting a less than molar equivalent of chlorine with 1,1,1-trifluoro-2-chloroethane vapor in a suitable reaction zone.
  • the gas stream exiting the reaction zone is condensed in a low temperature condenser and fed to a reboiler or to an intermediate point in a fractionating column.
  • the reboiler contents essentially consist of the 1,1,1-trifluoro-2,2-dichloroethane (b.p. 27° C.) and the 1,1,1-trifluoro-2-chloroethane (b.p. 6° C.), and same are next refluxed through a multiplate fractionating column at such a rate as desirably to maintain the overhead mix at a minimum of 99% of 1,1,1-trifluoro-2-chloroethane.
  • the 99% concentration of the CF 3 CH 2 Cl in the overhead mix is not essential; however, the higher its concentration and the lower the concentration of CF 3 CHCl 2 in such mix, the already minimal by-production of the undesired CF 3 CCl 3 is even more dramatically reduced.
  • the preferred ratio of CF 3 CH 2 Cl to CF 3 CHCl 2 in the mix is greater than 90:1.
  • the vapor exiting the fractionating column is mixed with incoming feed 1,1,1-trifluoro-2-chloroethane and chlorine, and passed through the reaction zone.
  • the reaction zone advantageously consists of a water-cooled condenser, maintained at a temperature sufficient to condense the 1,1,1-trifluoro-2,2-dichloroethane.
  • a well within this condenser jacket contains a white light source of a type which will photolyze chlorine.
  • the reaction zone is maintained at a temperature between about 5° and 175° C., and preferably is maintained between about 25° and 90° C., with room temperature [25° C.] being the most preferred.
  • the reaction zone consists of that volume in which a gaseous mixture containing CF 3 CH 2 Cl and chlorine are irradiated by light.
  • the function of the water-cooled condenser is to condense CF 3 CHCl 2 product and prevent it from entering the reaction zone, but to allow the lower boiling starting material (CF 3 CH 2 Cl) to pass into the reaction zone.
  • the flow rate of the reactant chlorine gas must be carefully regulated and controlled so that the molar ratio of chlorine to 1,1,1-trifluoro-2-chloroethane in the reaction zone does not exceed about 0.75, and which is preferably maintained in the range of between about 0.25 and 0.50.
  • the feed rate of fresh 1,1,1-trifluoro-2-chloroethane entering the reactor and the boil-up rate of same in the reboiler be adjusted to provide a residence time in the reaction zone of between about 0.1 and 60 seconds, preferably between about 1 and 5 seconds. Too short a residence time can lead to unreacted chlorine being entrained, condensed in the low temperature condenser, and carried into the reboiler.
  • the optimum residence time is in part dependent on the intensity of the light source.
  • the light source preferably has a radiation maximum between about 2700° and 5000 A, more preferably between about 3000 A and 4000 A, most preferably between about 3000 A and 3300 A, and desirably is filtered to minimize any radiation below 3000 A, which latter radiation is degradative and gives rise to the formation of the objectionable by-product.
  • any white light source filtered by Pyrex glass would be satisfactory; thus, the specific light source used in the photochlorination reaction is not critical.
  • the photochlorination reaction will take place while the reaction mixture is exposed to any source of actinic radiation.
  • Actinic radiation may be defined as the action of any light which effects chemical change. Hence, any form of light which effects chemical reaction may be employed, such as ordinary sunlight, ultraviolet light, commercial incandescent light and fluorescent light.
  • 1,1,1-trifluoro-2-chloroethane at 1.36 moles/hr. and chlorine at 0.68 moles/hr. are fed to the reaction zone and there photolyzed by means of filtered white light.
  • Unreacted 1,1,1-trifluoro-2-chloroethane passing through the reaction zone is condensed in the low temperature (-76° C.) condenser and returned to the reboiler, or to an intermediate point in the fractionating column.
  • 1,1,1-trifluoro-2,2-dichloroethane formed by the photochlorination is condensed in the water-cooled condenser (+15° C.) and flowed back down into the jacketed fractionating column.
  • the process of this invention unexpectedly provides surprisingly high yields of the desired 1,1,1-trifluoro-2,2-dichloroethane propellant, with only minimal formation of the more highly chlorinated 1,1,1-trifluoro-2,2,2-trichloroethane by-product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,1,1-trifluoro-2,2-dichloroethane [CF3 CHCl2 ] is prepared by contacting 1,1,1-trifluoro-2-chloroethane [CF3 CH2 Cl] with a less than molar equivalent of chlorine under conditions of photochemical chlorination. The CF3 CHCl2 is recovered substantially devoid of contaminating 1,1,1-trifluoro-2,2,2-trichloroethane [CF3 CCl3 ] by-product.

Description

BACKGROUND OF THE INVENTION
1. Field of the Invention:
The present invention relates to a process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane, namely, CF3 CHCl2, and, more especially, relates to the preparation of 1,1,1-trifluoro-2,2-dichloroethane by the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane [CF3 CH2 Cl] under certain critically defined reaction parameters.
2. Description of the Prior Art:
1,1,1-TRIFLUORO-2,2-DICHLOROETHANE, IS A KNOWN COMPOUND. This chlorofluorocarbon is of value as an aerosol propellant, particularly as a stratospherically safe aerosol propellant. And the thermal chlorination of 1,1,1-trifluoro-2-chloroethane too has been described in the prior art. Compare E. T. McBee et al, Ind. & Engineering Chem., 39, 409 (1947), wherein the thermal chlorination of 1,1,1-trifluoroethane [CF3 CH3 ] has been shown to proceed in the following stepwise manner:
CF.sub.3 CH.sub.3 + Cl.sub.2 → CF.sub.3 CHCl + HCl  (i)
CF.sub.3 CH.sub.2 Cl + Cl.sub.2 → CF.sub.3 CHCl.sub.2 + HCl (ii)
CF.sub.3 CHCl.sub.2 + Cl.sub.2 → CF.sub.3 CCl.sub.3 + HCl, (iii)
and wherein the reaction sequence [ii] can be said to represent the chlorination of interest.
However, McBee et at report that the molar ratio of chlorine to 1,1,1-trifluoroethane was approximately 1:1, and that the molar ratio of 1,1,1-trifluoro-2,2,2-trichloroethane [CF3 CCl3 ] to the subject 1,1,1-trifluoro-2,2-dichloroethane in their recovered product ranged from 1.1 to 1.4. This of course, reflects that the rate of chlorination of 1,1,1-trifluoro-2,2-dichloroethane to yield 1,1,1-trifluoro-2,2,2-trichloroethane is considerably faster than the rate of chlorination of 1,1,1-trifluoro-2-chloroethane to yield the desired 1,1,1-trifluoro-2,2-dichloroethane. Accordingly, there exists a need in the art to provide a facile process for the preparation of the valuable chlorofluorocarbon, 1,1,1-trifluoro-2,2-dichloroethane, with only minimal production of the more highly chlorinated by-product 1,1,1-trifluoro-2,2,2-trichloroethane.
SUMMARY OF THE INVENTION
It is, therefore, a primary object of the invention to provide a process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane which avoids the difficulties and shortcomings of the prior art processes.
Another object of the invention is to provide a process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane by the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane under certain critically defined reaction conditions.
Yet another object of the invention is to provide for the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane under such critically defined reaction conditions as to provide high yields of 1,1,1-trifluoro-2,2-dichloroethane with concomitant minimal [less than about 1%] by-production of the perhalogenated compound, 1,1,1-trifluoro-2,2,2-trichloroethane.
DETAILED DESCRIPTION OF THE INVENTION
It has now been determined according to the invention that the photochemical chlorination of 1,1,1-trifluoro-2-chloroethane can unexpectedly be conducted such as to provide high yields of 1,1,1-trifluoro-2,2-dichloroethane, with only minimal amounts [less than about 1 mole percent] of by-product 1,1,1-trifluoro-2,2,2-trichloroethane, by contacting a less than molar equivalent of chlorine with 1,1,1-trifluoro-2-chloroethane vapor in a suitable reaction zone. The gas stream exiting the reaction zone is condensed in a low temperature condenser and fed to a reboiler or to an intermediate point in a fractionating column. The reboiler contents essentially consist of the 1,1,1-trifluoro-2,2-dichloroethane (b.p. 27° C.) and the 1,1,1-trifluoro-2-chloroethane (b.p. 6° C.), and same are next refluxed through a multiplate fractionating column at such a rate as desirably to maintain the overhead mix at a minimum of 99% of 1,1,1-trifluoro-2-chloroethane. The 99% concentration of the CF3 CH2 Cl in the overhead mix is not essential; however, the higher its concentration and the lower the concentration of CF3 CHCl2 in such mix, the already minimal by-production of the undesired CF3 CCl3 is even more dramatically reduced. The preferred ratio of CF3 CH2 Cl to CF3 CHCl2 in the mix is greater than 90:1. The vapor exiting the fractionating column is mixed with incoming feed 1,1,1-trifluoro-2-chloroethane and chlorine, and passed through the reaction zone.
The reaction zone advantageously consists of a water-cooled condenser, maintained at a temperature sufficient to condense the 1,1,1-trifluoro-2,2-dichloroethane. A well within this condenser jacket contains a white light source of a type which will photolyze chlorine. Desirably the reaction zone is maintained at a temperature between about 5° and 175° C., and preferably is maintained between about 25° and 90° C., with room temperature [25° C.] being the most preferred. Thus, the reaction zone consists of that volume in which a gaseous mixture containing CF3 CH2 Cl and chlorine are irradiated by light. The function of the water-cooled condenser is to condense CF3 CHCl2 product and prevent it from entering the reaction zone, but to allow the lower boiling starting material (CF3 CH2 Cl) to pass into the reaction zone.
As heretofore mentioned, there are several critical parameters in the process of the invention which determine the ultimate ratio of the 1,1,1-trifluoro-2,2-dichloroethane to the by-product 1,1,1-trifluoro-2,2,2-trichloroethane:
First, the flow rate of the reactant chlorine gas must be carefully regulated and controlled so that the molar ratio of chlorine to 1,1,1-trifluoro-2-chloroethane in the reaction zone does not exceed about 0.75, and which is preferably maintained in the range of between about 0.25 and 0.50.
Second, it is virtually necessary that the feed rate of fresh 1,1,1-trifluoro-2-chloroethane entering the reactor and the boil-up rate of same in the reboiler be adjusted to provide a residence time in the reaction zone of between about 0.1 and 60 seconds, preferably between about 1 and 5 seconds. Too short a residence time can lead to unreacted chlorine being entrained, condensed in the low temperature condenser, and carried into the reboiler. The optimum residence time is in part dependent on the intensity of the light source. The light source preferably has a radiation maximum between about 2700° and 5000 A, more preferably between about 3000 A and 4000 A, most preferably between about 3000 A and 3300 A, and desirably is filtered to minimize any radiation below 3000 A, which latter radiation is degradative and gives rise to the formation of the objectionable by-product. No advantage accrues from using radiation with wavelengths above 5000 A. In general, any white light source filtered by Pyrex glass would be satisfactory; thus, the specific light source used in the photochlorination reaction is not critical. The photochlorination reaction will take place while the reaction mixture is exposed to any source of actinic radiation. Actinic radiation may be defined as the action of any light which effects chemical change. Hence, any form of light which effects chemical reaction may be employed, such as ordinary sunlight, ultraviolet light, commercial incandescent light and fluorescent light.
In order to further illustrate the present invention and the advantages thereof, the following specific example is given, it being understood that same is intended only as illustrative and in nowise limitative.
EXAMPLE
Utilizing the foregoing described equipment, 1,1,1-trifluoro-2-chloroethane at 1.36 moles/hr. and chlorine at 0.68 moles/hr. are fed to the reaction zone and there photolyzed by means of filtered white light. Unreacted 1,1,1-trifluoro-2-chloroethane passing through the reaction zone is condensed in the low temperature (-76° C.) condenser and returned to the reboiler, or to an intermediate point in the fractionating column. 1,1,1-trifluoro-2,2-dichloroethane formed by the photochlorination is condensed in the water-cooled condenser (+15° C.) and flowed back down into the jacketed fractionating column. After the first three hours of operation, a quantity of 1,1,1-trifluoro-2,2-dichloroethane has accumulated in the reboiler. The boil-up rate is adjusted to give a molar ratio of 1,1,1-trifluoro-2-chloroethane to chlorine in the reaction zone of 3:1. At the end of eight hours the reaction is terminated. Gas chromatographic analyses of the reboiler contents reveals the reaction product to consist of 1,1,1-trifluoro-2,2-dichloroethane, with less than about 1% 1,1,1-trifluoro-2,2,2-trichloroethane and 1,1,1-trifluoro-2-chloroethane starting material.
Thus, it will be appreciated that the process of this invention unexpectedly provides surprisingly high yields of the desired 1,1,1-trifluoro-2,2-dichloroethane propellant, with only minimal formation of the more highly chlorinated 1,1,1-trifluoro-2,2,2-trichloroethane by-product.
While there have been shown and described and pointed out the fundamental novel features of the invention as applied to the preferred embodiment, those skilled in the art will appreciate that various modifications, changes and omissions in the preparation of 1,1,1-trifluoro-2,2-dichloroethane illustrated and described can be made without departing from the spirit of the invention. It is the intention, therefore, to be limited only by the scope of the following claims.

Claims (14)

What is claimed is:
1. A process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane, comprising photochlorinating 1,1,1-trifluoro-2-chloroethane in a reaction zone with a less than molar equivalent of chlorine in the presence of actinic radiation, and with a residence time in the chlorine/1,1,1-trifluoro-2-chloroethane reaction zone of such duration that essentially no unreacted chlorine is entrained in the reaction effluent, but of insufficient duration as to effect other than minimal by-production of perhalogenated contaminant.
2. The process as defined by claim 1, wherein the less than molar equivalent of chlorine does not exceed about 0.75.
3. The process as defined by claim 2, wherein the less than molar equivalent of chlorine is in the range of between about 0.25 and 0.50.
4. The process as defined by claim 2, wherein the residence time in the reaction zone ranges from between about 0.1 and 60 seconds.
5. The process as defined by claim 4, wherein the residence time in the reaction zone ranges from between about 1 and 5 seconds.
6. The process as defined by claim 4, wherein the chlorine is white light photolyzed.
7. The process as defined by claim 6, wherein the white light has a radiation maximum of about 5000 A and is filtered to minimize radiation below about 3000 A.
8. The process as defined by claim 1, wherein the actinic radiation has a radiation maximum between about 2700 A and 5000 A.
9. The process as defined by claim 8, wherein the actinic radiation has a radiation maximum between about 3000 A and 4000 A.
10. The process as defined by claim 9, wherein the actinic radiation has a radiation maximum between about 3000 A and 3300 A.
11. The process as defined by claim 1 conducted at a temperature between 5 and 175° C.
12. The process as defined by claim 11 conducted at a temperature between 25° and 90° C.
13. The process as defined by claim 11 conducted at about room temperature.
14. The process as defined by claim 4, further including recycling a portion of the reaction zone effluent to the feed 1,1,1-trifluoro-2-chloroethane and chlorine.
US05/753,155 1976-12-21 1976-12-21 Preparation of 1,1,1-trifluoro-2,2-dichloroethane Expired - Lifetime US4060469A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US05/753,155 US4060469A (en) 1976-12-21 1976-12-21 Preparation of 1,1,1-trifluoro-2,2-dichloroethane
CA293,040A CA1076148A (en) 1976-12-21 1977-12-14 Preparation of 1,1,1-trifluoro-2,2,-dichloroethane
FR7737679A FR2375164A1 (en) 1976-12-21 1977-12-14 PROCESS FOR PREPARING 1,1,1-TRIFLUORO-2,2-DICHLOROETHANE
DE19772755828 DE2755828A1 (en) 1976-12-21 1977-12-15 Process for the preparation of 1,1,1-TRIFLUORO-2,2-DICHLORAETHANE
IT69847/77A IT1093049B (en) 1976-12-21 1977-12-20 PROCEDURE FOR THE PREPARATION OF I I I TRIFLUORO 2 2 DICHLOROETHANE
JP15250877A JPS5382711A (en) 1976-12-21 1977-12-20 Process for preparing 1*1*11trifluoroo2*22dichloroethane

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US05/753,155 US4060469A (en) 1976-12-21 1976-12-21 Preparation of 1,1,1-trifluoro-2,2-dichloroethane

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JP (1) JPS5382711A (en)
CA (1) CA1076148A (en)
DE (1) DE2755828A1 (en)
FR (1) FR2375164A1 (en)
IT (1) IT1093049B (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0344494A1 (en) * 1988-05-17 1989-12-06 Daikin Industries, Limited Process for production of 1,1,1-trifluoro-2,2-dichloroethane
EP0346612A1 (en) * 1988-05-17 1989-12-20 Daikin Industries, Limited Process for production of 1,1,1-trifluoro-2,2-dichloroethane
US4929318A (en) * 1987-09-22 1990-05-29 Daikin Industries Ltd. Process for preparing halogenated alkane
EP0402874A2 (en) * 1989-06-13 1990-12-19 AUSIMONT S.r.l. Process for preparing 1,1,1-trifluoro-2,2-dichloroethane
EP0407989A1 (en) * 1989-07-14 1991-01-16 Hoechst Aktiengesellschaft Method for the production of 1,1,1-trifluoro-2,2-dichloroethane by photochlorination
US5171899A (en) * 1988-05-17 1992-12-15 Daikin Industries Ltd. Process for production of 1,1,1-trifluoro-2,2-dichloroethane
US5254771A (en) * 1989-07-14 1993-10-19 Hoechst Aktiengesellschaft Process for the preparation of 1,1,1-trifluoro-2-2-dichloroethane under elevated pressure
WO1994003418A1 (en) * 1992-08-03 1994-02-17 Zeneca Limited Process for the preparation of 1,1,1-trichloro-2,2,2-trifluoroethane
TR27406A (en) * 1992-08-03 1995-03-09 Zeneca Ltd Chlorination process for the preparation of 1, -1, -1-trichlorotrifuoroetane.
US5414166A (en) * 1993-11-29 1995-05-09 Korea Institute Of Science And Technology Process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane
US5951830A (en) * 1996-10-18 1999-09-14 Elf Atochem S.A. Process for purification of hydrochlorofluoroethanes
WO2000076945A2 (en) * 1999-06-16 2000-12-21 Solvay Fluor Und Derivate Gmbh Uv-activated chlorination
US6229057B1 (en) 1993-07-26 2001-05-08 Zeneca Limited Chlorination process
US6551469B1 (en) 2001-11-27 2003-04-22 Honeywell International Photochlorination of 1,1,1,3,3-pentafluoropropane
US20080149472A1 (en) * 2004-12-22 2008-06-26 Velliyur Nott Mallikarjuna Rao Photochlorination and Fluorination Process for Preparation of Fluorine-Containing Hydrocarbons

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
DE3923248A1 (en) * 1989-07-14 1991-02-07 Hoechst Ag METHOD FOR PRODUCING 1,1,1-TRIFLUOR-2,2-DICHLORETHANE UNDER INCREASED PRESSURE

Citations (1)

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US3823195A (en) * 1971-12-27 1974-07-09 Monsanto Co Preparation of 1,1,2,3-tetrachloropropene from 1,2,3-trichloropropane

Patent Citations (1)

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US3823195A (en) * 1971-12-27 1974-07-09 Monsanto Co Preparation of 1,1,2,3-tetrachloropropene from 1,2,3-trichloropropane

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4929318A (en) * 1987-09-22 1990-05-29 Daikin Industries Ltd. Process for preparing halogenated alkane
US5315044A (en) * 1988-05-17 1994-05-24 Daikin Industries Ltd. Process for production of 1,1,1-trifluoro-2,2-dichloroethane
EP0344494A1 (en) * 1988-05-17 1989-12-06 Daikin Industries, Limited Process for production of 1,1,1-trifluoro-2,2-dichloroethane
EP0526908A2 (en) * 1988-05-17 1993-02-10 Daikin Industries, Limited Process for production of 1,1,1-trifluoro-2,2-dichloroethane
US5132473A (en) * 1988-05-17 1992-07-21 Daikin Industries, Ltd. Process for production of 1,1,1-trifluoro-2,2-dichloroethane
US5171899A (en) * 1988-05-17 1992-12-15 Daikin Industries Ltd. Process for production of 1,1,1-trifluoro-2,2-dichloroethane
EP0346612A1 (en) * 1988-05-17 1989-12-20 Daikin Industries, Limited Process for production of 1,1,1-trifluoro-2,2-dichloroethane
EP0526908A3 (en) * 1988-05-17 1993-02-24 Daikin Industries, Limited Process for production of 1,1,1-trifluoro-2,2-dichloroethane
EP0402874A3 (en) * 1989-06-13 1992-02-26 AUSIMONT S.r.l. Process for preparing 1,1,1-trifluoro-2,2-dichloroethane
EP0402874A2 (en) * 1989-06-13 1990-12-19 AUSIMONT S.r.l. Process for preparing 1,1,1-trifluoro-2,2-dichloroethane
EP0407989A1 (en) * 1989-07-14 1991-01-16 Hoechst Aktiengesellschaft Method for the production of 1,1,1-trifluoro-2,2-dichloroethane by photochlorination
US5254771A (en) * 1989-07-14 1993-10-19 Hoechst Aktiengesellschaft Process for the preparation of 1,1,1-trifluoro-2-2-dichloroethane under elevated pressure
US5414164A (en) * 1992-08-03 1995-05-09 Zeneca Limited Imperial Chemical House Chlorination process
CN1037961C (en) * 1992-08-03 1998-04-08 曾尼卡有限公司 Chlorination process
WO1994003418A1 (en) * 1992-08-03 1994-02-17 Zeneca Limited Process for the preparation of 1,1,1-trichloro-2,2,2-trifluoroethane
TR27406A (en) * 1992-08-03 1995-03-09 Zeneca Ltd Chlorination process for the preparation of 1, -1, -1-trichlorotrifuoroetane.
US6229057B1 (en) 1993-07-26 2001-05-08 Zeneca Limited Chlorination process
US5414166A (en) * 1993-11-29 1995-05-09 Korea Institute Of Science And Technology Process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane
US5951830A (en) * 1996-10-18 1999-09-14 Elf Atochem S.A. Process for purification of hydrochlorofluoroethanes
WO2000076945A2 (en) * 1999-06-16 2000-12-21 Solvay Fluor Und Derivate Gmbh Uv-activated chlorination
WO2000076945A3 (en) * 1999-06-16 2001-05-31 Solvay Fluor & Derivate Uv-activated chlorination
US20040016633A1 (en) * 1999-06-16 2004-01-29 Solvay Pharmaceuticals Gmbh UV-activated chlorination process
US20050101811A1 (en) * 1999-06-16 2005-05-12 Solvay Pharmaceuticals Gmbh UV-activated chlorination process
US7282120B2 (en) 1999-06-16 2007-10-16 Solvay Fluor Gmbh UV-activated chlorination process
US6551469B1 (en) 2001-11-27 2003-04-22 Honeywell International Photochlorination of 1,1,1,3,3-pentafluoropropane
US20080149472A1 (en) * 2004-12-22 2008-06-26 Velliyur Nott Mallikarjuna Rao Photochlorination and Fluorination Process for Preparation of Fluorine-Containing Hydrocarbons

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FR2375164A1 (en) 1978-07-21
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JPS5382711A (en) 1978-07-21
DE2755828A1 (en) 1978-06-22

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